Chemistry

Tim Funk

Chairperson/Associate Professor

Chemistry

Contact

Box

Campus Box 0393

Address

Science Center
Room 243
300 North Washington St.
Gettysburg, PA 17325-1400

Education

PhD California Institute of Technology, 2006
BS Gettysburg College, 2000

Academic Focus

synthetic organic chemistry, organometallic catalysis

Research Interests:

My students and I are interested in the broad field of synthetic organic chemistry. Our three main areas of research include: 1) the synthesis of complex structures inspired by nature; 2) the application of transition metal catalysts to organic chemistry; and 3) the synthesis of organic polymers with photocleavable crosslinks.

We are currently developing air-stable (cyclopentadienone)iron di- and tricarbonyl compounds for use as transfer hydrogenation and dehydrogenation catalysts. We discovered that these compounds catalyze a variety of oxidative and reductive transformations including alcohol oxidations, ketone and aldehyde reductions, oxidative cyclizations of diols, and selective epoxide ring-openings. Catalyst design is at the heart of our work, and we are constantly thriving to develop more active, air-stable iron catalysts. Additionally, we are interested in understanding the mechanism of these iron-catalyzed reactions to aid in further catalyst development. 

Recent Publications: (* denotes Gettysburg College undergraduate student)

  1. Funk, T. W.; *Mahoney, A. R.; *Sponenburg, R. A.; *Zimmerman, K. P.; *Kim, D. K.; *Harrison, E. E. Synthesis and Catalytic Activity of (3,4-Diphenylcyclopentadienone)Iron Tricarbonyl Compounds in Transfer Hydrogenations and Dehydrogenations. Organometallics 201837, 1133–1140. https://doi.org/10.1021/acs.organomet.8b00037
  2. *Plank, T. N.; *Drake, J. L.; *Kim, D. K.; Funk, T. W. Air-Stable, Nitrile-Ligated (Cyclopentadienone)iron Dicarbonyl Compounds as Transfer Reduction and Oxidation Catalysts. Advanced Synthesis & Catalysis 2012, 354, 597-601. https://doi.org/10.1002/adsc.201100896
  3. *Ziegler, D. T.; *Steffens, A. M.; Funk, T. W. Synthesis of alpha-Methyl Ketones by a Selective, Iridium-Catalyzed Cyclopropanol Ring-Opening Reaction. Tetrahedron Letters 2010, 51, 6726-6729. https://doi.org/10.1016/j.tetlet.2010.10.067
  4. *Moyer, S. A.; Funk, T. W. Air-Stable Iron Catalyst for the Oppenauer-Type Oxidation of Alcohols. Tetrahedron Letters 2010, 51, 5430-5433. https://doi.org/10.1016/j.tetlet.2010.08.004 
  5. Funk, T. W. Enantioselective Synthesis of 5-epi-Citreoviral Using Ruthenium-Catalyzed Asymmetric Ring-Closing Metathesis. Organic Letters 2009, 11, 4998-5001. https://doi.org/10.1021/ol901853t

Awarded External Grants

  • American Chemical Society Petroleum Research Fund, “Development and Application of Air-Stable, Shvo-Type Iron Catalysts,” 9/1/2012–8/31/2015.
  • Research Corporation for Science Advancement Single Investigator Cottrell College Science Award, “Transition Metal-Catalyzed Oxidations of Organic Molecules with Traditional Oxidants,” 7/2010–6/2012.

Courses Taught